用于苯并[b]氮杂卓和 1，3-共轭二烯歧化合成的催化剂控制型可切换形式逆-布赫纳反应

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2024-11-13 DOI:10.1016/j.tet.2024.134378

Zhaoxue Wang , Menghui Guo , Ping Wu , Rui Yan , Guili Zhao , Ming Liu , Yilei Xiao , Lingang Wu , Lei Xie

{"title":"用于苯并[b]氮杂卓和 1，3-共轭二烯歧化合成的催化剂控制型可切换形式逆-布赫纳反应","authors":"Zhaoxue Wang , Menghui Guo , Ping Wu , Rui Yan , Guili Zhao , Ming Liu , Yilei Xiao , Lingang Wu , Lei Xie","doi":"10.1016/j.tet.2024.134378","DOIUrl":null,"url":null,"abstract":"<div><div>Herein, a phosphine catalyst-controlled switchable formal retro-Büchner reaction of MBH carbonates with <em>N</em>-sulfonyl azaheptafulvenes has been successfully developed, which provides a divergent and efficient route to access valuable benzo[<em>b</em>]azepine and multiple substituted 1, 3-conjugated diene derivatives in moderate to great yields. Additionally, these methodologies are characterized by mild reaction conditions, absence of transition metal, easy operation, broad functional-group tolerance, and amenability to gram-scale synthesis.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"169 ","pages":"Article 134378"},"PeriodicalIF":2.1000,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Catalyst-controlled switchable formal retro-Büchner reaction for the divergent synthesis of benzo[b]azepines and 1, 3-conjugated dienes\",\"authors\":\"Zhaoxue Wang , Menghui Guo , Ping Wu , Rui Yan , Guili Zhao , Ming Liu , Yilei Xiao , Lingang Wu , Lei Xie\",\"doi\":\"10.1016/j.tet.2024.134378\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Herein, a phosphine catalyst-controlled switchable formal retro-Büchner reaction of MBH carbonates with <em>N</em>-sulfonyl azaheptafulvenes has been successfully developed, which provides a divergent and efficient route to access valuable benzo[<em>b</em>]azepine and multiple substituted 1, 3-conjugated diene derivatives in moderate to great yields. Additionally, these methodologies are characterized by mild reaction conditions, absence of transition metal, easy operation, broad functional-group tolerance, and amenability to gram-scale synthesis.</div></div>\",\"PeriodicalId\":437,\"journal\":{\"name\":\"Tetrahedron\",\"volume\":\"169 \",\"pages\":\"Article 134378\"},\"PeriodicalIF\":2.1000,\"publicationDate\":\"2024-11-13\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040402024005593\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402024005593","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

在此，我们成功开发了一种由膦催化剂控制的甲基溴碳酸盐与 N-磺酰基氮杂七烯烃的可切换形式逆-布赫纳反应，该反应提供了一条以中等至高产率获得有价值的苯并[b]氮杂卓和多种取代的 1，3-共轭二烯衍生物的不同而有效的途径。此外，这些方法的特点还包括反应条件温和、不含过渡金属、操作简便、对官能团有广泛的耐受性以及适合克级合成。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Catalyst-controlled switchable formal retro-Büchner reaction for the divergent synthesis of benzo[b]azepines and 1, 3-conjugated dienes

查看原文本刊更多论文

Catalyst-controlled switchable formal retro-Büchner reaction for the divergent synthesis of benzo[b]azepines and 1, 3-conjugated dienes

Herein, a phosphine catalyst-controlled switchable formal retro-Büchner reaction of MBH carbonates with N-sulfonyl azaheptafulvenes has been successfully developed, which provides a divergent and efficient route to access valuable benzo[b]azepine and multiple substituted 1, 3-conjugated diene derivatives in moderate to great yields. Additionally, these methodologies are characterized by mild reaction conditions, absence of transition metal, easy operation, broad functional-group tolerance, and amenability to gram-scale synthesis.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.